"You look...great."
"Thanks Tristan, you don't look too bad yourself."
"Naturally."
Of course there could never be a conversation with Tristan DuGrey where that egotistical sarcasm didn't come into play. He looked over at Paris and Alex sitting on the couch and saw something in his childhood friend that he'd never noticed before...a smile. Paris never smiled growing up, but Tristan knew that she still wasn't for him. He only wanted one person and he was finally getting that chance.
Walking out to Tristan's brand new Mustang, he attempted to take Rory's hand and she hesitantly accepted. Being a gentleman, Tristan opened the car door for Rory who was amazed at the person she was on a date with. She never expected Tristan to be the chivalrous type...sure he was charming and had been around, but he was still the same jerk who tortured her in high school.
"So Mary...are you ready for a night you'll never forget?"
"Planning ahead a little Tristan?"
"You know it."
Rory wanted to know what Tristan had planned for her, whatever it was she couldn't deny that she was nervous or that she wanted to kiss him again. They arrived at a little French café that looked extremely expensive and Rory let herself out of the car before Tristan had the chance to open the door. They went inside to find the hostess answering a phone call. After she wrote down the information of the caller she looked up and asked if Tristan had reservations.
"Yes...they're under DuGrey."
"Tristan DuGrey?" The hostess knew his name from somewhere and flashed him a seductive smile ignoring that Rory was even there.
"Do you have admirers everywhere?"
"Most likely. But none are as beautiful as the girl I'm with tonight."
Rory didn't know how to respond to that. She also wasn't sure if he meant it or if that was just a line to get in her pants. All she knew was Tristan was her date and for the rest of the night she would be there – with him.
During dinner the conversation topics stayed pretty basic...the last two years at Chilton, military school, Dean, Jess, but not very much about Tristan or his love life. He liked it that way...he didn't want to tell her that he couldn't keep a girlfriend because they all knew there was another girl on his mind.
"I can't believe it took me over four years to finally get you on a date."
"Why not make me sound like a prize?"
"I didn't mean it that way, Rory, honest. I just mean I've wanted to take you out since you turned me down for that study date your first day at Chilton. It's not like Tristan DuGrey to be turned down."
Rory just thought about how she was nothing but a prize to him. Now that he won and she accepted his date, that was it. This wasn't going to go anywhere and Rory would end up hurt. Tristan was going to leave just like Jess left. After dinner, they went to a little bakery that had coffee. Tristan could tell that ever since their conversation during dinner there was something going on with Rory. He didn't want to ruin anything; he wanted her to feel the way he did.
Before heading back to the Yale campus, Tristan decided to take Rory to a little beach he knew of. Rory looked around the beach, it was beautiful – she saw Long Island in the distance. All the kids at Chilton talked about summer houses in the Hamptons, she'd often wondered what it was like there. Her thoughts were interrupted by Tristan walking over next to her.
"Something's bothering you, Mary, you wanna fill me in?"
"Not really."
"Did I do something wrong?"
"It's nothing, Tristan, please can we go back?"
"I thought you'd like this place...we can talk."
Rory decided that she couldn't get out of being there with him, so she might as well have a conversation. The two sat on the beach staring into the beautiful water...a poetic scene for a couple. Rory didn't want to be a couple, she didn't trust Tristan...a romantic walk on the beach seemed like asking for sex to her.
"Tristan...can I ask you something?"
"You can ask me anything. What do you wanna know? How a rich boy could have a hard, chiseled body."
"Everything relates back to sex with you, Tristan, doesn't it?!"
"Everyone has something they're good at."
"So how many girls have you been with?"
Tristan thought about Rory's question...he honestly wasn't sure because of all those drunken weekends when he and Noah had snuck out of military school. The girls at Princeton and even those back at Chilton. He knew the answer would scare away the only girl he wanted.
"A few."
"That's all you're going to tell me?"
"What do you want to hear, Mary? That I sleep with any girl that I can get? Do you want to see me as Tristan the sex-craved bastard who will lie to girls to get into bed with him? Guess what, Mary, I have feelings too. You're right, let's get back to Yale."
Tristan's outburst hurt, Rory, but she knew that she was intruding. She was so curious...she'd only been with Dean and it was only a couple of times. Tristan was more experienced...he'd been younger his first time. Rory looked over at Tristan in the driver's seat with a really distant look.
All that Tristan could ask himself was "why?" Why did he blow up at her? He could've answered her or he could've just told her about the girls he really cared about. Maybe one day he'll tell her about his first time and the feelings he had for the girl it was with. After his little fit back at the beach he wasn't sure she'd ever want to talk to him again.
They arrived back at Yale and Tristan walked Rory back to her room. She wouldn't even look him in the eye when she said goodbye, she just stormed into the room to find Paris. Tristan, however, waited outside the room kicking himself for being so stupid.
Rory couldn't find Paris anywhere, and then she found a piece of paper sitting on her desk.

Rory – out with Alex for the night. Don't wait up. – Paris.

Rory tried to call her mother, but no one was answering the phone...most likely she was with Luke. She decided to call Luke's apartment, but not to see if her mother was there.
"Hello?"
"Can you come here now, please, I need someone to talk to,"Hel Rory's voice was breaking through her tears.
"I'm on my way."
With that Jess took his keys, left Luke a note, and headed for Yale.